


Let Mama Buy You a Drink

by Total_Mal



Series: Sir Dust Week Entries [1]
Category: Hazbin Hotel (Web Series)
Genre: DILF Pentious, Drag Queens, Gay Bar, Human AU, M/M
Language: English
Status: Completed
Published: 2020-09-10
Updated: 2020-09-10
Packaged: 2021-03-06 14:48:34
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,959
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26390665
Author URL: https://archiveofourown.org/users/Total_Mal/pseuds/Total_Mal
Summary: Entry for SirDust Week's Day 2 Prompt: Human AU.IF YOU READ, PLEASE COMMENT.Not Betaed
Relationships: Angel Dust/Sir Pentious (Hazbin Hotel)
Series: Sir Dust Week Entries [1]
Series URL: https://archiveofourown.org/series/1917982
Comments: 13
Kudos: 37





	Let Mama Buy You a Drink

Angel was used to seeing every type of person at the bar. The Village attracted gays from all walks of life and at this point in his career, he wasn’t gonna judge any rando that decided to take in a show as long as they weren’t causing any trouble for him and his girls.

But the well-dressed guy sitting alone with a half-drunk beer, looking mildly terrified (but also weirdly _sad)_ immediately drew his attention as he made his rounds through the crowd, teasing the regulars and accepting loose tips when offered.

Deciding to check in on the fella, he adjusted the set of rubber boobs filling out the top of his green sequin dress and sauntered over, catching the older man’s eye on approach and giving him a knowing wink. Immediately the stranger stiffened and tried to look away, using his curtain of long straight black hair (streaked with just a bit of silvery gray) to hide his face.

Angel chuckled and took the bar stool next to the soon to be silver-fox, tousling the thick curls of his fire-engine red wig as they tumbled over his exposed shoulders. “Well _you’re_ certainly a new face,” he said with a grin, leaning one elbow on the bar to rest his chin in his gloved hand, careful not to smear the thick coating of drag makeup he'd spent the last _hour_ applying to his face. “First time?” he teased, gesturing to the man’s gray wool jacket (clearly tailored to that trim figure and more akin to something you’d find off _Wall Street_ rather than Houston).

The man cleared his throat and fiddled with his own hair, the silky strands slipping off his broad shoulders in an effortless way that most models would envy. “Is it _that_ obvious?” he asked, his nervous voice tinged with a distinctly British accent as he took another sip of his beer.

Angel just laughed and adjusted the long hem of his dress, making sure the hip-length slit exposed a good-sized window of thigh as he crossed his legs. “Eh, I’m better than most at spottin’ newbies.” He winked and looked the other man over, noting the _woman's_ wedding ring that sat on a chain around the man’s throat, barely visible under the black pinstripe tie tucked into his blazer. Ah, _now_ it was more obvious: a widower looking to get back into the dating game, but too middle-aged and _clueless_ to do more than google the nearest gay bar. Cute, but definitely sad. Could probably use more than a single beer at any rate.  
  
“So did ya expect the drag show or just come for the go-go dancers?” Angel teased, continuing to take in all the details of the man's face and expensive-looking outfit. He'd always liked the fellas who put in _some_ effort even if it was a little too much for the occasion (and _boy_ was this guy over-dressed for a drag show).

The man took another swallow of beer and finally met Angel’s eyes in earnest under the club's purposefully dim colored lights. “I actually didn’t know there was a performance going on tonight to be perfectly honest. But I’m here now so I might as well stay and watch.” He gave a weak laugh and shook his head as he adjusted the fit of his cuffs. “It would be a _waste_ of the entry fee to just go home.”

“So what’d ya come here for if not the show?” Angel asked, tapping the counter when the bartender walked by in a request for his usual. “We don’t normally get guys like you unless they’re a lil’ on the _curious_ side of things.” Though those fellas were some of the _best_ lays. They were always just so damn earnest and eager to try things out, especially the ones who spent most of their life in the closet. It was like they had something to _prove_ when they finally grew the nuts to step out. 

The man immediately flushed and Angel couldn’t help but grin all the wider as he watched the color stain those well defined cheek-bones. “I figured it couldn’t hurt to explore _new venues…_ ” the stranger said after a moment, thumbing over the peeling label on his beer with one hand while the other pulled out a Blackberry (dear lord did they even still _make_ those?) from inside his blazer to check the time.

Angel nodded as the bartender slid him a vodka cranberry, switching the part of his legs and noting the way the other man’s eye-line immediately dropped from the phone to the way the slit of his dress exposed Angel's olive-toned thighs. “Well if it's _new_ ya want, you're certainly in the right place,” Angel said with a wink, sipping the cocktail (careful not to smudge his lipstick) and batting his long fake eyelashes at the stranger. “What’s your name, handsome?”

The man pursed his lips and then reached one arm up to tuck his hair back behind his ear, exposing the strong column of his throat and adam’s apple. “Simon,” he said after a moment, his dark eyes still looking over Angel as if he couldn’t quite make up his mind about whether or not he liked what he saw.

 _“Simon,_ huh?” Angel clicked his tongue and said, “Well babe, you can call me _Angel.”_ He took another sip of his drink as he watched the man (Simon) lift his beer and finish the rest of it in a swallow that had no right being _that_ smooth coming from a man dressed to the nines. “Got enough liquid courage to survive the night?”

Simon just snorted and shook his head, putting the bottle back down before fiddling with a nice silver rolex on his wrist. “I’ll need something _far_ stronger than beer for that,” he murmured as he pushed the empty bottle away, letting the bartender snatch it up and toss it into the recycling with a clatter as they passed.

Chuckling, Angel stood with his drink and gently touched the other man’s shoulder with his opposite hand, smoothing his fingers over the tight weave of the fabric. “Lemme order ya the house special then. That shit’s _guaranteed_ ta get ya greased in the wheels.” He took another long slurp from his cocktail and added, “Tell Trey it’s from Angie and he’ll hook ya up.”

Simon went stiff under his touch and Angel smiled, slowly removing his fingers so as to not spook him further. “No need ta be _jumpy._ You’re in good hands here.” He gave the man another sultry wink and said, “But I gotta head ta the back. My number is startin’ soon and as we say in the biz: the show must go on."

Nodding, Simon looked at Angel, his eyes drifting around before ultimately resting back on Angel's face. “Well, I don’t know what the expression is for doing _drag,_ but in theatre, it’s break a leg.” Simon cleared his throat and offered him a soft handsome smile before adding, “It was a pleasure to meet you, Angel.”

“Such a _gentleman,”_ Angel said, swallowing the rest of his cocktail and leaving the empty glass on the bar for the tender to put on his tab. “Hope you enjoy the show, _Simon.”_ He blew the other man a kiss, enjoying the deep blush it earned him before turning to head backstage, making sure to exaggerate the sway of his narrow hips with each stomp of his stilettos.

Once he was behind the curtain, Angel caught sight of Cherri standing on top of a rusted out ladder, fixing the lights that lined the back of the stage. “Hey, you finally made it!” he said with a grin, leaning back and resting a hand on his hip as he watched her adjust the angle of the bulb. "Need any help up there?"

“Nah, I got it,” she called before slowly stepping backwards down the rungs, her boots scraping against the metal. She jumped the last two steps and grinned, wiping her messy strawberry blonde bangs back out of her face before adjusting the fit of her ripped fingerless gloves. “Ugh, woulda been here sooner, but my new neighbor is such an anal _dickbag._ His fucking cat got into my apartment last night and instead of being grateful for keeping her safe, he went off on me acting like I _stole_ the damn thing.” She huffed and shook her head before taking the ladder and moving it out of the way to rest against the worn brick wall behind them.

Angel winced and followed her, making sure the heavy metal didn't tip back over and on top of her. “Well shit, maybe you should just keep it next time? Clearly it likes you more than him.”

Cherri snickered and nodded in agreement. _“Right?”_ she said as some of the newer drag queens began to line up at the stairs leading onto the stage, still adjusting their hair and dresses in the cracked mirror that hung crookedly against the wall. “So, how’s the crowd? Anyone stirrin' shit?” she asked, gesturing to the closed blue velvet curtain.

“Mmm, nah it's mostly the regulars, though I did just talk with a pretty cute DILF at the bar,” Angel said with a laugh as he thought about how adorably blushy the older man got with just a bit of flirtation. “Nervous as fuck and clearly out of his depths, but y’know, I like helpin’ guys learn how to test the waters.” He gave a suggestive eyebrow waggle and Cherri laughed, smacking his shoulder.

"Suuure. It's all about helping _them,"_ she cackled as Angel stepped forward and peeked through a small gap in the curtains. A quick glance to the bar confirmed that Simon was still there, the club's ridiculously neon blue signature cocktail in one hand and his phone in the other as he attempted to take a selfie.

Pulling back, Angel watched as Cherri checked over the rest of the lighting equipment, making sure all the cords and wires were kept out of the way and were properly taped down. "Alright, you guys should be good to go. We'll wanna get that one fixture replaced soon, but it'll hold up for tonight." She gestured to the bulb she'd been messing with and Angel nodded. 

"Thanks, babe," Angel said as she walked off the stage and toward the technician's closet to go and sign in her equipment. He turned back to the curtain and had to slap a hand over his mouth to keep himself from giggling as he watched other man sip at his drink, looking mildly disgusted at first before taking another taste and seeming to settle into the flavor.

Smiling, Angel pulled away from the curtain and checked himself once more in the mirror off to the side of the stage where the baby queens were waiting, buzzing with excitement and more than a few frayed nerves. "Alright ladies, there's a lotta folks out there, but don't be scared. Angel's gonna take care of ya," he told them with a confident flick of his wrist. "Just remember, _you're_ the goddamn star and there ain't nobody that's gonna stomp on stage ta show you up. Got it?"

They nodded and Angel chuckled as their over-sized wigs bounced with the motion, barely managing to stay on their heads despite the multitude of bobby pins buried throughout the synthetic weave.

He grinned and stepped back, shoving the first girl up the stairs (the rest quickly following to avoid receiving the same treatment). "You'll do fine, babes! C'mon, let's give these fellas a show!"

As each of his little drag babies did their numbers, Angel watched from just out of sight, a deep sense of pride growing in his chest as the girls left the stage to thunderous applause from the supportive audience. Of course their performances _were_ on the mediocre end, but that would get better with time and practice. The club's most loyal patrons were always generous on a debut night and gave the new girls plenty of tips so he wasn't too worried about having to console a weeping queen in the dressing room at the end of the show.

Of course, now that his lil' birds had left the nest, it was _his_ turn to strut his stuff.

When the music for last number began to fade, he exhaled, taking a deep breath as his heart started to pounded in his chest. Then his name was announced and the crowd's excited hooting and hollering hit _hard,_ boosting his adrenaline faster than _any_ drug. 

Stepping under the lights, Angel struck a dynamic pose, hip jutting out to expose the long slit of his dress as he peered at the crowd, affecting a dismissive attitude. Raising his microphone, he flipped the bangs of his wig and grinned. "Well _well_...were you all good to my little _chickadees?"_ he purred into the mic, slowly strutting across the stage in his six inch platform stilettos.

His eyes swept the crowd in a smooth pass even as he was unable to distinguish any individual faces due to how bright the spotlight was. "It's _Mama's_ turn now." He gave a sultry wink, earning more than a few hoots before laughing. "Oh you fellas really know how ta make a _lady_ feel _wanted."_

He snapped his fingers and the music started up behind him, the speakers blaring out _"When You're Good To Mama"._ Angel began to mouth the words, dancing across the stage a bit before descending the steps to playfully interact with his regulars, taking tips with a glide of his free hand as the spotlight worked to follow him around the club.

Angel caught sight of Simon at the bar and he smirked, continuing to lipsync as he sauntered over and touched the side of the man's face with his gloved hand. _"There's a lot of favors, I'm prepared to do,"_ he gave the other man a flirty little wink before lowering his hand to grip Simon's tie, sliding his fingers along the length of the silk. _"You do one for Mama, she'll do one for **you."**_

The other man visibly swallowed and Angel almost laughed as he released the tie, moving to the next man at the bar and lifting his hat before dropping it unceremoniously back onto the countertop with a practiced flick of his wrist.

After his solo, he joined in a few group numbers with several of his more veteran queens, dancing across the stage and generally just enjoying the thrill of performing.

Every time he caught Simon's eye, Angel saw the other man take a drink as if he had to steel himself from the intensity of the look alone. It brought a mild heat to the performance, knowing that he'd so thoroughly seduced this guy with little more than light conversation and a few winks, but Angel didn't let it distract him. He was there to entertain the people, not just one (admittedly) very cute DILF he'd only just met.   
  
When all his routines were wrapped up, he headed back stage again, stealing a cigarette from Cherri as she smoked on a stool, lighting the end with the glowing tip of hers. "Mmmm, think I should go for it?" Angel mused as she mindlessly flicked through her phone next to him.  
  
"Go for _what?"_

Angel dragged his wig and cap off his head, scratching through his sandy brown hair to get it back to its normal frizz and floof. "Takin' that classic Jaguar out for a spin," Angel jerked his thumb back toward the stage as he stuffed the cig into his mouth, not caring as red lipstick smeared over the outside paper. "He was lookin' at me _all_ night and I get the feelin' that he's had enough drinks by now to be a bit more loose in the cage if ya know what I'm sayin'."  
  
Cherri snorted and glanced up at him, standing and tucking her phone back into her ripped skinny jeans. "Well, if he doesn't seem like complete trash, why not? Go feed that daddy kink of yours, Angie," she said, giving him a playful elbow as he smoked, blowing out a plume into the air above them.   
  
Chuckling, Angel said, "I'm gonna get changed first. Make sure he ain't turned off once the titties are gone, y'know?" He cupped the rubber breasts and gave a quick shimmy before heading back to the dressing room to clean up and get changed.  
  
By the time he came out in his normal black booty shorts, white v-neck, and striped jacket, the club had grown dark and more traditional house music was playing. The dance floor and bar were also now significantly more crowded, but Simon was still at his stool, empty drink in one hand and his hilariously outdated phone in the other.   
  
Angel grinned and sidled up to him, tapping the other man's shoulder. "Hey stranger. You look awfully familiar," he teased, enjoying the brief look of confusion that flashed across Simon's face before recognition slowly dawned. "Enjoy the show? I know _I_ did."  
  
Simon smiled and set the glass down at the bar. "It was certainly a lot more fun than I expected." He glanced to Angel's thigh-high heels and added, "I was impressed you managed to dance _and_ keep your balance in heels that high, but I see now that this is probably fairly routine for you."   
  
"What can I say, I like bein' a tall bitch," Angel said as he gave the other man a shameless once-over. Maybe it was the alcohol finally loosening him up, but rather than shy away from the sultry look, Simon actually stretched out, straightening his shoulders and puffing up his broad chest. The older man instantly reminded him of a peacock and Angel couldn't help but give the other man a flirtatious wink of approval. "Ya got plans? Can't imagine a guy like you is ready ta cut up the dance floor in pants _that_ tight."   
  
"I'm not much of a dancer," Simon admitted, glancing over his shoulder to stare at the bouncing crowd. "I might just call a cab and head home, though...I was wondering if I could perhaps get a schedule?" He cleared his throat and reached up to adjust his tie as he turned back to look at Angel. "For any future shows."  
  
Angel raised an eyebrow and said, _"Oh?_ Interested in comin' back?" he asked, leaning one hand on the bar as he rested the opposite against his hip. "The schedule should be on the website. We update it every month so the line-up's pretty accurate."  
  
Simon nodded and added, "Actually, I'm unable to connect to the internet at the moment. The service in here is _terrible."_ He laughed and fiddled with his loose hair. "Would you be so kind as to text it to me?"  
  
Angel blinked. Oh, that was fucking _adorable._

"Tryin' ta get my number, handsome?" he asked, enjoying the way the other man immediately tensed at being called out. "I'll give ya points for creativity," Angel added with a wink, reaching out and taking Simon's Blackberry from him, opening up his list of contacts before entering the number he kept specifically for hookups (being sure to label it _♡Angel♡)_  
  
Handing the device back, he let his fingers brush the older man's and Angel couldn't help but laugh as Simon nearly fumbled and dropped his own phone (thankfully catching it again before it slipped out of his grasp). "Oops, _butterfingers!"_  
  
Before Simon could do more than straighten and give an embarrassed huff, Angel heard Cherri call for him over the pulsing club music. "Hey Angie, I'm gonna head out. I got a ton of bookings tomorrow and-" Cherri paused, stopping short behind Angel as she glanced over his shoulder. "What the _fuck_ are you doing here, _old man!?"_  
  
Simon's smile fell as his eyes met Cherri's, lips flattening into a bitter line. "I could say the same to you, _missy."_  
  
Caught in the middle, Angel blinked and stepped back, very much confused now. "Uh, you guys know each other?" he asked, looking to his friend for literally any goddamn explanation she was willing to offer.   
  
"Y'know the _annoying_ neighbor I was telling you about?" Cherri said, crossing both arms over her chest as she lifted her chin toward Simon who just scowled right back as he slipped his Blackberry into his blazer. "Small fucking world I guess..."

She paused and then her eyes widened. "Wait...is _this_ the fuckin' DILF you were-" She cut herself off and groaned, lifting one hand to rub down the side of her face. _"Ang...."_  
  
 _"DILF?"_ Simon repeated as Angel just sighed and took Cherri by the shoulder, turning her away from the bar. 

"Hey, I didn’t know!" He hissed, meeting her eyes under the fringe of her hair. "Besides, it's not like we were gonna go on a _date_ or some shit. You know I ain’t into-" He glanced back to the bar and frowned, seeing Simon was gone with only a few bills left by the empty glass to signal his departure. "Shit..."

"Not that I mean to cockblock, but he's an _asshole,_ Ang. You're better off finding another old fart to diddle," Cherri muttered, shifting her red pleather jacket up onto her shoulders. "If you really want to get your dick wet, _fine_. Just don't tell me about it." She sighed and added, "Normally I don't mind the gossip, but I _live_ below that fucker."

Angel sighed and shook his head. "It's fine, Cherri. It ain't that serious." Though it did suck because Simon was _really_ cute, but sometimes that was just how the cookie crumbled. There were always other guys and Angel never had much trouble finding someone to sleep around with. "Lemme walk ya out at least, babe. Make sure ya don’t get trampled by all the drunks."

He escorted Cherri through the main floor and to the front, waving as he watched her shove through the crowd that was lined up to get inside. 

Once she was out of sight, he went to go back into the club, only for his burner phone to buzz in his pocket. He frowned and pulled it out, noting a single text from an unfamiliar number.

**_"My sincerest apologies for the abrupt exit, but I had no desire to start an argument with my ill-mannered neighbor at the bar."_ **

There was a brief pause before the phone buzzed again. ** _"This is Simon by the way."_**

Angel chuckled and was about to respond, but then the thread updated a _third_ time. **_"Unless I was given a fake number, in which case, I'm sorry for the spam. Feel free to ignore/delete these messages."_**

God what a _dork_. Angel smiled and typed back, _"Hey, I get it. Shit got awkward."_ He paused and added, _"I'm off shift now tho. You got anywhere 2 be?"_

There was a break and Angel was almost ready to put away the phone when the next message populated underneath his. 

**_"There's nowhere I need to be, however I do believe I owe a certain Mama a favor for being kind enough to buy me a drink earlier this evening."_ **

Angel blinked and then grinned before copying and pasting the address of his favorite dive bar into the chat. _"Y'know if you spice it up for Mama, she'll get **hot** for you."_

He added an eggplant emoji and several water splashes afterward, only to receive a confused series of question marks from Simon in turn, making him cackle as he headed down into the nearest subway terminal to catch a train to the bar. 

Looks like he might get to test drive that Jaguar after all.

**Author's Note:**

> Please comment?


End file.
